Established at the outset of the punk rock boom, Stiff signed various punk rock and new wave acts such as Nick Lowe, the Damned, Lene Lovich, Wreckless Eric, Elvis Costello, Ian Dury, and Devo, also signing artists with significant crossover appeal such as Motörhead, Larry Wallis and Mick Farren.

In the 1980s, with most of their early signings having moved on, the label found commercial success with Madness, The Pogues, Tracey Ullman, The Belle Stars, Kirsty MacColl and others.

[2] Razor & Tie, a division of the Concord Music Group, holds the American rights to the Stiff catalogue.

Robinson had briefly worked for Jimi Hendrix in the late 1960s and also managed minor pub rock band Brinsley Schwarz in the early 1970s, in which Nick Lowe was the bassist, vocalist and main songwriter; while Riviera had been an early manager for another pub rock band, Dr. Feelgood, from Essex.

Its first release, on 14 August 1976, was a single (in the normal 7" vinyl 45 rpm format) by Nick Lowe, "So It Goes", B-side "Heart of the City", with the striking catalogue number BUY 1.

[7] Robinson and Riviera used money from their Advancedale management company to finance the release of what is generally accepted as the United Kingdom's first punk single, "New Rose" by The Damned, on 22 October 1976.

Early in 1977, Stiff Records picked up speed, signing Wreckless Eric, Ian Dury, and Elvis Costello, who had once been a part-time roadie for Brinsley Schwarz.

Riviera's departure coincided with the end of the "5 Live Stiffs Tour", which showcased emerging star Ian Dury.

Island was very short of money at the time and Robinson had to lend it £1,000,000 to fund the share purchase and pay the payroll.

It then released a string of well-received albums of new work from legacy Stiff artists, including as Wreckless Eric, Henry Priestman, Any Trouble, and Chris Difford.

The first tour, known as the Live Stiffs Tour or 5 Live Stiffs (3 October – 5 November 1977), comprised five bands: Elvis Costello and The Attractions, Ian Dury and the Blockheads, Wreckless Eric and The New Rockets, Nick Lowe's Last Chicken in the Shop, and Larry Wallis's Psychedelic Rowdies.

There were 18 musicians on the tour, several doubling up, e.g. Dury playing drums for Wreckless Eric while the last two "bands" had the same line up (Nick Lowe, Larry Wallis, Dave Edmunds, Terry Williams, Pete Thomas and Penny Tobin).

Costello played mostly new material and cover versions, rather than numbers from his recently released album My Aim is True, so the gigs usually ended with most of the artists on stage performing Dury's "Sex & Drugs & Rock & Roll".